- Base promoted air oxidation of 13β-ethyl-11-methylenegon-4-en-17-one
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The structure of 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-16β,17-diol (3, 16β-OH desogestrel), a by-product obtained in the last step of the synthesis of desogestrel (1) by reaction of monolithium acetylide-ethylenediamine complex with 13β-e
- Compostella, Federica,Colombo, Diego,Modica, Emilia,Antonio Scala,Toma, Lucio,Bovio, Bruna,Ronchetti, Fiamma
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Read Online
- PROCESS AND NEW INTERMEDIATES FOR THE PREPARATION OF 11-METHYLENE STEROIDS
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The invention relates to a process for the preparation of 11 -methylene steroids through selective olefination of the ketone at position 11. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as Etonogestrel and Desogestrel.
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Page/Page column 36; 37
(2017/09/19)
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- Intermediate used for synthesis of desogestrel, and preparation method and application thereof
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The invention discloses an intermediate used for synthesis of desogestrel, and a preparation method and application thereof. The intermediate has a general chemical structural formula as described in the specification, wherein a substituting group R is selected from the group consisting of hydrogen, methyl or ethyl. The intermediate is prepared by subjecting a compound as shown in a formula 2 to selective protection reaction for a 3-carbonyl group by using dihydric alcohol, wherein the dihydric alcohol has a chemical structural formula as described in the specification, wherein R is selected from the group consisting of hydrogen, methyl or ethyl; and a reaction formula of the dihydric alcohol is described in the specification. The method for the synthesis of the desogestrel by employing the intermediate comprises a reaction route as described in the specification.
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Paragraph 0062; 0063; 0064; 0065; 0066
(2016/10/08)
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- Desogestrel and its new process for preparation of the intermediate compounds
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The invention relates to a preparation process for desogestrel and a novel intermediate compound thereof. In the prior art, 11-bit methylene is introduced through a wittig reaction in the preparation process of desogestrel, and a large quantity of environmental pollutants are produced in the reaction. In the preparation process for desogestrel and the novel intermediate compound thereof provided by the invention, the 11-bit methylene is introduced through an addition reaction, so that the problem of excessive discharge of pollutants is solved, reaction time is shortened, yield is increased, and industrial production is facilitated.
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Paragraph 0050-0052
(2017/03/28)
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- Desogestrel preparation method and midbody compound
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The invention relates to a novel steroidal compound and application of the novel steroidal compound in a desogestrel preparation process. The novel compound easy to separate is obtained through 17-bit selective ethynylation of 13beta-ethyl pregnane-4, 5-alkene-11, 17-diketone. When the compound is used for preparing desogestrel, simplicity and convenience in operation are achieved, and yield is high.
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Paragraph 0057; 0058; 0059; 0060
(2016/10/17)
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- COMBINED SYNTHESIS ROUTE FOR ETONOGESTREL AND DESOGESTREL
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The present invention relates to a synthesis route and to steroid derivatives of general formula VI and VII useful in the synthesis of desogestrel and etonogestrel.
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- TOTAL SYNTHESIS OF ENANTIOPURE DESOGESTREL
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The present invention relates to a total synthesis of desogestrel and derivatives thereof, and to intermediate compounds of this synthesis.
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Page/Page column 37-38
(2009/04/25)
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- Enantioselective total synthesis of the oral contraceptive desogestrel by a double heck reaction
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A novel enantioselective total synthesis of the oral contraceptive desogestrel (2) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone 7 led to the chiral bicycle 6 which was used for a diastereoselective intermolecular Heck reaction with vinyliodide 5 to give 15. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give 4, from which the synthesis of desogestrel (2) was furnished.
- Tietze, Lutz F.,Krimmelbein, Ilga K.
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experimental part
p. 1541 - 1551
(2009/04/04)
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- PROCESS AND NEW INTERMEDIATES FOR THE PREPARATION OF STEROIDS WITH A PROGESTOGEN ACTIVITY
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The present invention relates to a new process of synthesis and to some new intermediates for the preparation of steroids with progestogen activity, more particularly, for the preparation of Desogestrel of formula (I). Said process is characterized by the regioselective reduction of the compound of formula (II) to give the intermediate of formula (III).
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- Pharmaceutical combined preparation, kit and method for hormonal contraception
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PCT No. PCT/DE96/01192 Sec. 371 Date Jun. 3, 1998 Sec. 102(e) Date Jun. 3, 1998 PCT Filed Jun. 27, 1996 PCT Pub. No. WO97/01342 PCT Pub. Date Jan. 16, 1997The present invention describes a two-stage pharmaceutical combined preparation for hormonal contraception containing at least 30 daily unit doses, which preparation, in its first stage, comprises as hormonal active ingredient a combination of an oestrogen preparation and, in a dose that is at least sufficient to inhibit ovulation, a gestagen preparation, in single stage form and, in the second stage comprises as hormonal active ingredient an oestrogen preparation only, wherein the first stage comprises a minimum of 25 and a maximum of 77 daily discrete or continuous unit doses and the second stage comprises 5, 6 or 7 daily discrete or continuous unit doses, and wherein the total number of daily units is equal to the total number of days of the desired cycle of a minimum of 30 and a maximum of 84 days. This combined preparation, in the form of a monthly pack, which is used for female fertility control, permits as low as possible an oestrogen content in each individual unit dose and also has a low total hormone content per cycle of administration, with high contraceptive reliability, low incidence of follicle development, and satisfactory cycle control with reliable avoidance of intermediate bleeding as well as undesired side effects.
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- A short enantioselective total synthesis of the third-generation oral contraceptive desogestrel
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Desogestrel (1) has been synthesized enantioselectively by a 14-step process from the known and readily available precursor 3, as outlined in Chart 2. At the heart of this process is the short, convergent, and stereocontrolled method for forming the tetracyclic ring system and the critical 11-exomethylene function, that is, the sequence of steps 6 → 8 → → 12. All steps of the synthesis proceed in good yield.
- Corey,Huang, Alan X.
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p. 710 - 714
(2007/10/03)
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- Pharmaceutical combination preparation for hormonal contraception
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The invention provides a pharmaceutical combination preparation with two hormone components in a packaging unit and intended for time-sequential oral administration, comprising a number of daily dosage units physically separate and individually removable in the packaging unit, whereby as a hormonal active ingredient a first hormone component contains in combination an estrogen preparation and in at least a dosage that is sufficient to inhibit ovulation a gestagen preparation, and as a hormonal active ingredient the second hormone component contains only an estrogen preparation, whereby the first hormone component comprises 23 or 24 daily units and the second hormone component comprises 4, 3 or 2 daily units, and between these two hormone components, 2 or 1 active ingredient-free daily units are present or 2 or 1 blank pill days are indicated, and the total number of hormone daily units and the active ingredient-free daily units or the blank pill days is equal to the total number of days of the desired cycle, but at least 28 days in length. This combination preparation is useful for female birth control, and allows for an estrogen content that is as low as possible in each individual dosage unit and also has a low total hormone content per administration cycle, with high contraceptive reliability, low incidence of follicular development, and satisfactory cycle control, with reliable avoidance of intracyclic menstrual bleeding as well as of undesirable side-effects.
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- Steroid intermediate products and method of their production
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The invention is directed to novel steroid intermediate products of general formula I STR1 The steroid intermediate products which can be isolated according to the invention are suitable for the synthesis of 13-ethyl-11-methylene-18,19-bisnor-17α-pregn-4-en-20-in-17-ol (desogestrel). Further, processes for producing the steroid intermediate products of general formula I are described. The olefination of the 11-oxo steroids is carried out under the influence of ultrasound.
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- Pharmaceutical combination preparation for hormonal contraception
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A pharmaceutical combination preparation with two hormone components that are manufactured physically separately in a packaging unit and that are intended for time-sequential oral administration, which in each case consist of a number of daily dosage units that are placed physically separately and are individually removable in the packaging unit. As a hormonal active ingredient, a first hormone component contains in combination an estrogen preparation and, in at least a dosage that is sufficient to inhibit ovulation, a gestagen preparation, and as a hormonal active ingredient the second hormone component contains only an estrogen preparation. The first hormone component comprises 23 or 24 daily units and the second hormone component comprises 4 to 10 daily units. The total number of hormone daily units is equal to the total number of days of the desired cycle, but at least 28 days in length. This combination preparation is used for female birth control, and allows for an estrogen content that is as low as possible in each individual dosage unit and also has a low total hormone content per administration cycle, with high contraceptive reliability, low incidence of follicular development, and satisfactory cycle control, with reliable avoidance of intracyclic menstrual bleeding as well as of undesirable side-effects.
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- Anti-glaucomatous pharmaceutical composition and the process for obtaining them
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The invention relates to the domain of medicinal chemistry. It concerns more particularly that of the preparation of pharmaceutical compositions for ocular use. A subject of the invention is pharmaceutical compositions for ocular use characterized in that they contain at least one selected compound of steroidal structure in combination with or admixed with a pharmaceutically-acceptable, inert carrier or vehicle. The compositions according to the invention are intended to the treatment of glaucoma.
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- Synthesis of 13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (Desogestrel) and its Main Metabolite 3-Oxo-Desogestrel
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A synthesis of the steroid hormone desogestrel (25) from the 18a-homo steroid 1 is described. 25 was transformed into 3-oxo-desogestrel (28) by allyl oxidation.
- Schwarz, Sigfrid,Ring, Sven,Weber, Gisela,Teichmueller, Gerhard,Palme, Hans-Joachim,et al.
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p. 10709 - 10720
(2007/10/02)
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- A partial synthesis of 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (desogestrel) based upon intramolecular oxidation of an 11β-hydroxy-19-norsteroid to the 18->11β-lactone
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A partial synthesis of the 13-ethyl-18-norsteroid desogestrel is reported.The key step in the synthesis is the intramolecular oxidation of 11β-hydroxyestr-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal) 3 with Pb(OAc)4 and iodine to 3,3:17,17-bis-11β-hydroxyestr-5-en-18-oic acid γ-lactone 2.The 13-COOH group was then converted into a 13-ethyl group by a Grignard reaction with methylmagnesium bromide followed by Wolff-Kishner reduction of the 13-acetyl group thus formed.
- Heuvel, M. J. van den,Bokhoven, C. W. van,Jongh, H. P. de,Zeelen, F. J.
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p. 331 - 334
(2007/10/02)
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